The Waitress

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Sweet petite Ashley finds out she's submissive the rough way.
2.9k words
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Part 1 of the 10 part series

Updated 10/31/2022
Created 01/01/2002
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*********

She was having a hard time to make ends meet. Her little son Tim was attending a private elementary school, his father paying for the tuition, when suddenly the bastard stopped sending the alimony and disappeared from view. She had complained to the court but they said little could be done if the man wasn't located first, so she should hire a private investigator. Yeah? With what money? Assholes!!

... When she was having trouble to pay the bills, the morons asked her to hire a detective... What was she going to do?

If she ever found Richard, she would just kill him, that's for sure!! The son of a bitch!!

Tim would lose his school year if something didn't happen very soon...

Her friend and fellow coworker Trish found her crying in the groceries little room.

"Listen, Ashley, the world isn't going to crumble just because your kid loses the year.

He can restart once you improve your situation"- she said encouragingly.

"I will not allow that to happen!"- she yelled in pain.

Trish looked at her, startled.

"Alright, alright, you will not allow that to happen... How?"

"I don't know!!"- she said in frustration.

Trish was pensive for a moment.

"You know that sometimes I go out with the customers, and then they give me some extra money. And when they come back here they give me better tips. That makes for more money in the end, to compensate for the ridiculous salary that son of a bitch Sam pays us..."

Ashley looked at her friend with disbelieving eyes.

"Are you suggesting that I... I can't believe this!"- she shouted again.

"Cool down. Just a friendly suggestion. You need the money and you know it. Besides, they ain't gonna take anything that hasn't been taken already"

"What?! Are you my friend or what? Are you asking me to become a WHORE just like..."- she stopped dead cold in her tracks, but Trish was no fool.

"Just like I am? Well, thanks, honey, I appreciate the compliment. At least, I don't have to be all anguished about the rent, and my kids will have their education, even if my asshole husband goes away with some other slut... just like me"- Trish left Ashley alone with her thoughts.

"Come on, accept me an invitation. I don't bite. Well, yes I do, but... softly"

He had a charming smile, and a big built. Most truck drivers were big. She smiled shyly.

"I'm sorry, I'm married"

"Not anymore, honey!... so don't tell lies. She's divorced, Harry"

Ashley's mouth was open with embarrassment.

"Well, that's good news!"- said Harry smiling.

"Excuse us"- said Ashley and took Trish away from the table.

"What the hell you think you're doing?! Embarrassing me like that?"

"Just bringing you back into reality, you silly... What is that story about you married?

It's been two years since you got a divorce!!"

"It is none of your goddamned business!"

***

"But I will pay. Please don't..."- Ashley was crying in front of the school's director.

"I'm sorry, Mrs. Thropp, if we don't have the tuition paid by Monday, your son will lose his place in class. As you know, that means he'll lose the year too. I'm sorry"

She was desperate. She had lost her own schooling due to poverty also. Now it was going to happen to his only son.

***

Another day in hell...

"Hello, sweetheart"- Harry greeted her, cheerful as usual.

She swallowed hard. She was trembling when she spoke.

"What... Would you like your coffee strong as usual?"

"Yes. What happens to you? You look nervous"

"Nevermind, sir" - she swallowed hard again.- "Remember when you invited me to... go out with you?"

"Of course I do"- He suddenly turned serious, in anticipation, silently admiring the voluptuous forms in front of him. Was he going to be lucky tonight? He had been desiring her, as she was the most attractive of all the waitresses at Sam's, and the only one there who wasn't known for fucking the truck drivers. That alone made her even more desirable, to be able to break her down into doing what she didn't want to do... Ashley was a 26 year old natural red head, of alabaster white skin, about 36D, he calculated... she had big breasts!... She was small ( barely 5' 3" barefoot, to his impressive 6' 2" ) but fat- assed and with a slim waist that invited to hold her there. And her somewhat short legs had stupendous thighs that led to a prominent crotch... "Why, sweetheart?" - he could have eased the way for her, but he chose not to. It turned him on the prospect of her having to ask for a date herself...

He was about to regret the move, her eyes showed panic. But she went on. She breathed deeply and asked:

"Would you still go out with me?"

It was a delightful moment, to have this gorgeous piece of ass asking for a date..

"Sure, honey. You won't have to ask twice. When?"

"Now..."- the simple word came out too quickly and too emotional, and she resented her own lack of self- control. She thought, I wasn't made for this. I can't even talk.

"Now I have little time. I have to hit to road, up to Missouri. But if you have time for a quickie one right now, I'll be generous with you..." - he said simply.

She blushed immediately at the proposal. So this was it, no romance at all, just the wanting to fuck her and that was that. She felt pity for herself. She remembered then that she wasn't going to be a whore for pleasure.

"I'm sorry to ask, but... how generous? I have a problem, and I..."

"You won't complain"- he interrupted her, smiling again- "Can you go out now?"

"No. But my shift is over in less than an hour"

***

Ashley went into the trailer's cabin, feeling uncomfortable as hell, even though it was a very cozy cabin, with all the gadgets imaginable, even a little freezer and color TV.

The worst thing was that the other waitresses were watching with eagle eyes, from the restaurant. Now they would make mock of her everyday. She used to be the only one who didn't fuck the truck drivers.

- Well, I guess not anymore...- she thought, a couple of tears struggling to come out of her eyes.

He had huge hands and arms, and his touch was somewhat rude. He said he had little time tonight, and proceeded to get rid of her clothes first, while she blushed intensely and couldn't look him in the eye.

She had to look at his penis in amazement. It was huge!! But what was she expecting? A man of such a big built wasn't going to have a small pecker... It was very thick and long, with an enormous purple head, it look menacing as hell!

He noticed her eyes opened as plates watching his cock.

"Come on, despite his looks, he's very friendly, I assure you"- he said in jest.

"If I were you, I would be proud of such a penis too"- she said- "The problem is I'm not going to take that into me. You'd kill me. Sorry"- she said gravely.

She took her blouse and started to dress again.

"What? Come on! I have put it inside 18 year olds and they didn't chicken out. It won't hurt you, I assure you. This is silly"

"Sorry, sir. I just won't take that... thing inside me"

She was about to get off the trailer still barefoot, when she noticed that all the bitches were still looking from the restaurant windows. Even old Sam was discreetly peeping, the old bastard.

"Shit"- she thought in despair- "if I miss this one, they will be merciless in their jokes. They'll say I'm not woman enough. I'm sure those silly cows have already taken him... Besides, I need to make money badly"

"Come on, sweetheart. I'll be especially tender with you"- he encouraged her.

"Alright"- she said hopelessly- "Please call the coroner while I am dying split in two"- she said lugubriously.

"That's my girl!!"

"I like my girls to be in all fours for me, honey"

"I am not your girl"- she said with her last vestiges of pride.

"You are... tonight"

He took her in his strong big arms and easily made her point her bare ass to him, while her head and arms were down against the mattress.

He proceeded to caress his ass cheeks first, with expert hands. After a minute, she was very moist, to her surprise. Well, it's been so long since a man fondled me, - she thought-, so no wonder. Then he gave her ass cheeks some few soft slaps. She felt her cheeks get hot, while her pussy was now drooling moisture down her thighs.

"I hope them bitches won't come to have a close look" - she thought- "I'd be embarrassed to death!"

"Oh you're going to kill me!!" - she protested.

He had begun to go into her, and he honored his promise to be gentle, but still she felt she was being torn apart... and it was only the head and a bit more that had gotten inside her cunt!!

"Take it easy, honey. Soon you'll be taking all of it easily..."- he said.

... And so it happened. But it wasn't easy. Despite her reassurances, she felt she was being split apart, and if it weren't for her badly needing the money, she would have run away from him, she thought.

He let his enormous shaft to just lie there inside her for a while, the full impressive length of it at nearly 13 inches!... and as thick as a baby's arm, the bloody thing...

"There, honey"- he helped her feel herself with her fingers that all the huge shaft was now inside her cunt. She couldn't believe she had taken all of that meat in her twat.

Then he took her by the hips and started to fuck her, slowly at first. After a few moments she felt a big orgasm numbing her... he kept moving slowly, making her have the longest climax she could remember. Then he started to move faster and harder, hitting her mercilessly with each thrust. She started to feel acute pain, and was going to protest, when another orgasm, much stronger than the first one, went through her body like an electric shock, from her head to her toes. She moaned and shook uncontrollably, and couldn't think anymore...

Ashley was senseless, numb and mesmerized by the powerful cock that had taken her as prey. She couldn't think no more. She could just hear her own moans and her own pleas to be fucked even harder. Her fingers were clinched, grabbing the pillow, in an instinctive attempt to ease the pain in her crotch. Her toes were nervously twitching.

He kept fucking her hard for what seemed like an eternity, until she felt she was going to lose conscience. She lost count of the orgasms she had, each one apparently stronger and wilder than the previous one, until she was a mess of moans, cries and sweat. Then, she could take no more. The male had subjugated the female... Yes, she had to ask for mercy...

"Please... it's too much. I can't take no more. Please..."

He smiled arrogantly. Another cunt tamed by his wondrous cock...

"Alright, honey".

He went out of her with a pop. He was pleased to see that her inner thighs were a mess of her own juices, and the cabin now could be taken for a sea food store, judging by the smell!... and it was all HER smell and her cum...

While she couldn't avoid cumming for who knows how many times... he didn't come at all. He took pride at his self control, the true measure of how much of a man you are.

Besides, he had other plans in mind.

She turned around and fell on her back, exhausted, her eyes blinded by her uncontrollable sweating.

"Ok, honey, you had your pleasure, now you care to give me mine?"

She cleaned her sweaty eyes with the covers.

"What do you mean your pleasure? Didn't you have enough already, fucking me like crazy?"

"Nope. I didn't come"

"You didn't... What you mean you didn't"

"I mean I didn't. I wanna come in your mouth"

The mere thought of having to swallow the semen of a stranger made her turned her face to the side with revulsion. She didn't even do it for her husband, much less for this cocky truck driver!

"What? You're crazy! I won't do that. You already had me, now just be as generous as you said you was going to be, and let's say goodnight!"

"No way, darling. All of the others do it, why shouldn't you? I'll be generous, but only if you're generous too. Don't tell me you have never sucked cock before"

She felt infuriated by his vulgar words... but after spreading her ass open for him, she was in no good position to pretend to be a classy lady anymore, she thought in dismay... And she still didn't have his money in her hands.

"Alright..." - she gave up.

"That's my girl!! And one more thing: you can spit it out if you want, but if you want a real nice 'tip'... you'll have to swallow, precious"

So there was she, struggling to take his huge cock in her pouty lips, breathing with difficulty. So big he was, the bastard! And it grew even more, once she had taken a third of it in her sweet mouth ( she could never take it all, it was too big for that, and she wouldn't even try it ). Then he took her by her beautiful red hair ( she was a natural red hair of Irish ascendance ), and directed her moves in and out of his shaft.

The feel of her cherry lips sucking his monstrous dong, the sight of this pretty chick kneeling in front of him, submitting to his manly desires, aroused him so much that even a man with his amazing self control couldn't hold it no more. After just a couple of minutes he came inside her mouth, and poor Ashley had to suddenly deal with a

torrent of semen going down her throat. On top of it all, the bastard had the balls of a bull, and a big load of hot cum in them! She couldn't help gasping and gaggling, and couldn't hold all of his seemingly endless cum inside of her. A big part of it slid down her lips, and slipped down her breasts.

Remembering what he had just said, she apologized, once having swallowed most of his cum, once she could talk:

"I... I'm sorry. I really tried to take it all... but you come like a fucking horse! I'm sorry, I... please be generous... please..."

The sight of her saying this to him, while his cum was still sliding down her lips was comical, but also very exciting. If she only knew how much of a wanton woman she was, made for pleasure. She just needed some "coaching", just like all little sluts do, he thought...

"Don't worry, sweetheart. And... thanks! I have to say you just gave me the blow job of my life!"

She blushed again, still dumb- founded and hardly believing all that she was doing.

"Here we go, honey"- he looked in his wallet and gave her a roll of bills- " and if you want to be my little slut more often, you won't have to worry about money anymore...

Your only worry may well come to be to give me pleasure... How about that, baby?"

Her rebellious nature was about to propel her to shout some insult at him for calling her his little slut, but she thought better. The money was in her hands finally, and she was in no position to play decent lady anymore. She would have to live with the embarrassment of actually having been a whore. Yes, he was right, she now was a slut...

"Thank you"- she said, mechanically. She was spent, and her groins were aching very painfully now. She put up her shoes and went out of the cabin feeling very dizzy, her knees threatening to fail her.

She barely paid attention to his last words for the night.

"You're a royal piece of ass, honey. See you, I gotta make this baby run fast now, if I want to be in St. Louis in time! Bye!"- saying this, he ignited the engine.

She barely heard that because she was counting the money with disbelieving eyes.

He was VERY generous indeed. $ 500 bucks!! Her mouth was open in amazement and joy. If all the drivers were as nice as Harry, soon she'd be able to get little Tim back in school for good!!... That's when she noticed the laughter of the other waitresses.

God, she forgot about them for a moment. That was a mistake. They saw her counting the bills, and now she was going to be the subject of many crude jokes about her ability to do "business"... Even Sam, the old fart, looked at her disapprovingly as she was counting the money. How could she be so stupid? Shit!! "Oh to hell with them!!"

She thought- "I made very good money, and that's all that matters"

To be continued...

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